Lincomycin

Identification

Summary

Lincomycin is an antibiotic indicated only for the treatment of serious infections and is typically reserved for use in cases of penicillin allergy or where penicillin is inappropriate.

Brand Names
Lincocin
Generic Name
Lincomycin
DrugBank Accession Number
DB01627
Background

Lincomycin is a lincosamide antibiotic first isolated from the soil bacterium Streptomyces lincolnensis in Lincoln, Nebraska.2 Clinical use of lincomycin has largely been superseded by its semisynthetic derivative clindamycin due to its higher efficacy and a wider range of susceptible organisms, though lincomycin remains in use.1,2

Lincomycin was approved by the FDA on December 29, 1964.10

Type
Small Molecule
Groups
Approved, Vet approved
Structure
Weight
Average: 406.54
Monoisotopic: 406.213757997
Chemical Formula
C18H34N2O6S
Synonyms
  • Cillimycin
  • LCM
  • Lincomicina
  • Lincomycin
  • Lincomycine
  • Lincomycinum
External IDs
  • U-10,149
  • U-10149

Pharmacology

Indication

Lincomycin is indicated for the treatment of serious bacterial infections by susceptible strains of streptococci, pneumococci, and staphylococci in patients who are allergic to penicillins or for situations in which a penicillin is deemed inappropriate. As with all antibacterial agents, lincomycin should only be used to treat infections proven or strongly suspected to be caused by susceptible bacteria.10

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofSerious bacterial infection•••••••••••••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Lincomycin is a lincosamide antibiotic derived as a natural fermentation product from Streptomyces lincolnensis. Like clindamycin, lincomycin is active against Gram-positive cocci and bacilli as well as Gram-negative cocci and some other organisms such as Haemophilus spp. It is also effective against anaerobic bacteria, though in this regard clindamycin is generally more potent.1,2 Prescribing information highlights that the range of clinically confirmed effectiveness is largely limited to Staphylococcus spp. and Streptococcus spp., with additional activity noted in vitro.10

Lincomycin should be used with caution due to its association with severe cutaneous hypersensitivity reactions such as Stevens-Johnson syndrome, toxic epidermal necrolysis, erythema multiforme, and acute generalized exanthematous pustulosis, and its potential to precipitate Clostridium difficile associated diarrhea (CDAD), which may lead to fatal colitis. Special care should therefore be exercised when used in elderly patients, individuals with a history of gastrointestinal disease, and those with a history of asthma or significant allergies. Lincomycin for injection may contain benzyl alcohol as a preservative, which has been associated with gasping syndrome in pediatric patients. The serum half-life is extended in patients with hepatic/renal impairment and may require dose adjustments and additional monitoring. Like all antibiotics, lincomycin use may cause overgrowth of non-susceptible organisms, which should be considered.10

Mechanism of action

Lincomycin contains the unusual amino acid moiety propyl hygric acid linked to the sugar moiety α-methylthiolincosamine (α-MTL) that, like other lincosamides, functions as a structural analogue of the 3' end of L-Pro-Met-tRNA and deacylated-tRNA to interact with the 23S rRNA of the 50S bacterial ribosomal subunit.1,2 Detailed investigations into the mechanism of the related lincosamide clindamycin suggested a two-phase binding, instantaneously to the A-site with a shift in equilibrium towards the P-site over several seconds.3,4,5 This shift appears to be due to rotation of the propyl hygric acid moiety, while the α-MTL remains relatively stationary.5,6 Recent crystal structures of lincomycin in complex with the 50S ribosomal subunit of Staphylococcus aureus show that the α-MTL moiety forms hydrogen bonds with C2611, A2058, G2505, A2059, and G2503 of the 23S rRNA while the propyl hygric acid moiety interacts only through van der Waals contacts, suggesting it may be free to rotate similar to clindamycin.6 This mechanism is supported by the observation that the most common resistance mechanism, which also affects macrolides and streptogramin B (MSLB resistance) involves methylation of A2058; other resistance mechanisms similarly target residues such as A2058, A2059, and C2611.2,6

TargetActionsOrganism
A23S ribosomal RNA
binder
Enteric bacteria and other eubacteria
Absorption

A 600 mg dose of lincomycin administered over two hours intravenously results in an average Cmax of 15.9 μg/mL while the same dose given by intramuscular injection produces an average Cmax of 11.6 μg/mL after 60 minutes.10 Lincomycin administered intramuscularly to healthy adult male volunteers in doses between 600 and 1500 mg had an AUC0-∞ between 92.22 and 159.91 μg*h/mL.7 A similar study using intravenous infusion of 600-2400 mg lincomycin found AUC0-∞ values between 72.5 and 212.8 μg*h/mL.8 Overall, the AUC increases disproportionally to dose.7,8

Volume of distribution

Lincomycin administered intravenously to healthy adult males had a steady-state volume of distribution of 63.8 ± 23.8, 78.8 ± 17.0, and 105.1 ± 43.1 L for 600, 1200, and 2400 mg doses, respectively.8

Protein binding

Lincomycin serum protein binding varies greatly depending on the dose, ranging from 28 to 86% in one study,8 and generally decreases with increasing serum concentration suggesting saturable binding.7,8 It has been suggested that lincomycin, like clindamycin, is primarily bound to α1-acid glycoprotein,8 which is consistent with later studies in humans and animals.9

Metabolism

Lincomycin metabolism is poorly defined, though the primary product recovered following administration in humans is unchanged lincomycin.11

Route of elimination

Following a 600 mg dose of lincomycin given either intramuscularly or intravenously, the urinary excretion ranges from 1.8-30.3% of the administered dose. Bile is also thought to be an important route of elimination. Dose adjustments are required in patients with either renal or hepatic impairment.10

Half-life

Lincomycin has a biological half-life of 5.4 ± 1.0 hours following intramuscular or intravenous administration, which is prolonged in patients with impaired hepatic or renal function.10

Clearance

Lincomycin administered intravenously to healthy adult males had a clearance of 9.9 ± 2.5, 10.0 ± 2.0, and 11.8 ± 2.4 L/h for 600, 1200, and 2400 mg doses, respectively.8

Adverse Effects
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Toxicity

Toxicity information regarding lincomycin is not readily available. Patients experiencing an overdose are at an increased risk of severe adverse effects such as gastrointestinal effects including colitis, secondary infections, and severe hypersensitivity reactions. Symptomatic and supportive measures are recommended. It is important to note that hemodialysis and peritoneal dialysis do not appreciably affect lincomycin serum concentrations.10

Pathways
PathwayCategory
Lincomycin Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AcenocoumarolThe risk or severity of bleeding can be increased when Lincomycin is combined with Acenocoumarol.
AcetophenazineAcetophenazine may increase the neurotoxic activities of Lincomycin.
AlimemazineAlimemazine may increase the neurotoxic activities of Lincomycin.
AmbroxolThe risk or severity of methemoglobinemia can be increased when Lincomycin is combined with Ambroxol.
AmisulprideLincomycin may increase the neurotoxic activities of Amisulpride.
Food Interactions
No interactions found.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Lincomycin hydrochlorideGCW8Y9936L859-18-7POUMFISTNHIPTI-BOMBIWCESA-N
Lincomycin hydrochloride monohydrateM6T05Z2B687179-49-9LFZGYTBWUHCAKF-DCNJEFSFSA-N
International/Other Brands
Lincobect / Lincorex
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
LincocinSolution300 mg / mLIntramuscular; IntravenousPfizer Canada Ulc1964-12-312016-05-06Canada flag
LincocinInjection, solution300 mg/1mLIntramuscular; Intravenous; SubconjunctivalPharmacia & Upjohn Company LLC2021-08-172021-08-17US flag
LincocinCapsule500 mgOralPfizer Canada Ulc1964-12-312006-08-02Canada flag
LincocinInjection, solution300 mg/1mLIntramuscular; Intravenous; SubconjunctivalPharmacia & Upjohn Company LLC1964-12-29Not applicableUS flag
LincocinInjection, solution300 mg/1mLIntramuscular; Intravenous; SubconjunctivalPharmacia & Upjohn Company LLC2023-04-18Not applicableUS flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
LincomycinInjection, solution300 mg/1mLIntramuscular; IntravenousSlate Run Pharmaceuticals, Llc2022-12-30Not applicableUS flag
LincomycinInjection, solution300 mg/1mLIntramuscular; Intravenous; SubconjunctivalPraxgen Pharmaceuticals LLC2021-03-30Not applicableUS flag
LincomycinInjection, solution300 mg/1mLIntramuscular; Intravenous; SubconjunctivalXGen Pharmaceuticals DJB, Inc.2015-07-05Not applicableUS flag
LincomycinInjection, solution3000 mg/10mLIntramuscular; IntravenousArmas Pharmaceuticals Inc.2023-05-05Not applicableUS flag
LincomycinInjection, solution300 mg/1mLIntramuscular; IntravenousSlate Run Pharmaceuticals, Llc2022-12-30Not applicableUS flag

Categories

ATC Codes
J01FF02 — Lincomycin
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as proline and derivatives. These are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Proline and derivatives
Alternative Parents
Alpha amino acid amides / Thioglycosides / Pyrrolidinecarboxamides / Monosaccharides / N-alkylpyrrolidines / Oxanes / Monothioacetals / Trialkylamines / Secondary carboxylic acid amides / Secondary alcohols
show 8 more
Substituents
Alcohol / Aliphatic heteromonocyclic compound / Alpha-amino acid amide / Amine / Azacycle / Carbonyl group / Carboxamide group / Glycosyl compound / Hydrocarbon derivative / Monosaccharide
show 23 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
monocarboxylic acid amide, pyrrolidinecarboxamide, L-proline derivative, carbohydrate-containing antibiotic, S-glycosyl compound (CHEBI:6472)
Affected organisms
  • Enteric bacteria and other eubacteria

Chemical Identifiers

UNII
BOD072YW0F
CAS number
154-21-2
InChI Key
OJMMVQQUTAEWLP-KIDUDLJLSA-N
InChI
InChI=1S/C18H34N2O6S/c1-5-6-10-7-11(20(3)8-10)17(25)19-12(9(2)21)16-14(23)13(22)15(24)18(26-16)27-4/h9-16,18,21-24H,5-8H2,1-4H3,(H,19,25)/t9-,10-,11+,12-,13+,14-,15-,16-,18-/m1/s1
IUPAC Name
(2S,4R)-N-[(1R,2R)-2-hydroxy-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(methylsulfanyl)oxan-2-yl]propyl]-1-methyl-4-propylpyrrolidine-2-carboxamide
SMILES
[H][C@]1(C[C@@H](CCC)CN1C)C(=O)N[C@H]([C@@H](C)O)[C@H]1O[C@H](SC)[C@H](O)[C@@H](O)[C@H]1O

References

Synthesis Reference

Alexander D. Argoudelis, David W. Stroman, "Process of producing lincomycin nucleotides." U.S. Patent US4464466, issued June, 1972.

US4464466
General References
  1. Spizek J, Rezanka T: Lincomycin, clindamycin and their applications. Appl Microbiol Biotechnol. 2004 May;64(4):455-64. doi: 10.1007/s00253-003-1545-7. Epub 2004 Feb 5. [Article]
  2. Spizek J, Rezanka T: Lincosamides: Chemical structure, biosynthesis, mechanism of action, resistance, and applications. Biochem Pharmacol. 2017 Jun 1;133:20-28. doi: 10.1016/j.bcp.2016.12.001. Epub 2016 Dec 7. [Article]
  3. Verdier L, Bertho G, Gharbi-Benarous J, Girault JP: Lincomycin and clindamycin conformations. A fragment shared by macrolides, ketolides and lincosamides determined from TRNOE ribosome-bound conformations. Bioorg Med Chem. 2000 Jun;8(6):1225-43. doi: 10.1016/s0968-0896(00)00081-x. [Article]
  4. Kouvela EC, Petropoulos AD, Kalpaxis DL: Unraveling new features of clindamycin interaction with functional ribosomes and dependence of the drug potency on polyamines. J Biol Chem. 2006 Aug 11;281(32):23103-10. doi: 10.1074/jbc.M603263200. Epub 2006 Jun 7. [Article]
  5. Kostopoulou ON, Papadopoulos G, Kouvela EC, Kalpaxis DL: Clindamycin binding to ribosomes revisited: foot printing and computational detection of two binding sites within the peptidyl transferase center. Pharmazie. 2013 Jul;68(7):616-21. [Article]
  6. Matzov D, Eyal Z, Benhamou RI, Shalev-Benami M, Halfon Y, Krupkin M, Zimmerman E, Rozenberg H, Bashan A, Fridman M, Yonath A: Structural insights of lincosamides targeting the ribosome of Staphylococcus aureus. Nucleic Acids Res. 2017 Sep 29;45(17):10284-10292. doi: 10.1093/nar/gkx658. [Article]
  7. Smith RB, Lummis WL, Monovich RE, DeSante KA: Lincomycin serum and saliva concentrations after intramuscular injection of high doses. J Clin Pharmacol. 1981 Oct;21(10):411-7. doi: 10.1002/j.1552-4604.1981.tb01742.x. [Article]
  8. Gwilt PR, Smith RB: Protein binding and pharmacokinetics of lincomycin following intravenous administration of high doses. J Clin Pharmacol. 1986 Feb;26(2):87-90. doi: 10.1002/j.1552-4604.1986.tb02911.x. [Article]
  9. Son DS, Osabe M, Shimoda M, Kokue E: Contribution of alpha 1-acid glycoprotein to species difference in lincosamides-plasma protein binding kinetics. J Vet Pharmacol Ther. 1998 Feb;21(1):34-40. doi: 10.1046/j.1365-2885.1998.00111.x. [Article]
  10. FDA Approved Drug Products: Lincocin (lincomycin) injection [Link]
  11. EMA Committee Report Lincomycin Sep 1998 [Link]
  12. Cayman Chemical: lincomycin MSDS [Link]
KEGG Drug
D00223
KEGG Compound
C06812
PubChem Compound
3000540
PubChem Substance
46506668
ChemSpider
2272112
BindingDB
50335522
RxNav
6398
ChEBI
6472
ChEMBL
CHEMBL1447
ZINC
ZINC000003982483
Therapeutic Targets Database
DAP000839
PharmGKB
PA164749212
PDBe Ligand
3QB
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Lincomycin
PDB Entries
4wh5 / 5hkv / 8a5i / 8cgk

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4RecruitingTreatmentBacteremia caused by Staphylococcus Aureus1
1CompletedNot AvailableBacterial Infections1
0TerminatedTreatmentOsteomyelitis1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Bimeda Inc.
  • Carlisle Laboratories Inc.
  • Clint Pharmaceutical Inc.
  • Dispensing Solutions
  • Keene Pharmaceuticals Inc.
  • Llorens Pharmaceutical
  • Martin Surgical Supply
  • Medisca Inc.
  • Nord Ost Corp.
  • Pharmacia Inc.
  • Preferred Pharmaceuticals Inc.
  • Raz Co. Inc.
Dosage Forms
FormRouteStrength
Solution300.000 mg
SolutionIntravenous600.000 mg
SolutionIntramuscular600 mg
SolutionIntramuscular; Intravenous600 mg
SolutionIntramuscular300.000 mg
PowderOral
Powder
CapsuleOral
CapsuleOral500.000 mg
Injection, solutionIntramuscular; Intravenous; Subconjunctival300 mg/1mL
Injection, solutionParenteral300 MG
Injection, solutionParenteral600 MG
SolutionIntramuscular; Intravenous300 mg / mL
SolutionIntravenous300 mg
InjectionIntramuscular; Intravenous600 mg/2ml
InjectionIntramuscular; Intravenous600 mg
CapsuleOral250 mg
Injection, solutionIntramuscular; Intravenous300 mg/1mL
Injection, solutionIntramuscular; Intravenous3000 mg/10mL
Injection, solutionIntramuscular; Intravenous600 mg/2mL
InjectionIntramuscular; Intravenous300 mg/ml
Solution
InjectionParenteral300 mg/ml
Injection, solutionIntramuscular; Intravenous
CapsuleOral500.00 mg
SyrupOral
CapsuleOral500 MG
InjectionIntramuscular; Intravenous
Injection, solution300 mg/1ml
Solution300 mg/1ml
Prices
Unit descriptionCostUnit
Lincocin 300 mg/ml vial7.79USD ml
Lincomycin hcl powder3.29USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)187-190https://www.scbt.com/p/lincomycin-b-hydrochloride-11021-35-5
water solubilityfreely solubleFDA Label
logP0.56HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility29.3 mg/mLALOGPS
logP0.5ALOGPS
logP-0.32Chemaxon
logS-1.1ALOGPS
pKa (Strongest Acidic)12.37Chemaxon
pKa (Strongest Basic)7.97Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count7Chemaxon
Hydrogen Donor Count5Chemaxon
Polar Surface Area122.49 Å2Chemaxon
Rotatable Bond Count7Chemaxon
Refractivity102.67 m3·mol-1Chemaxon
Polarizability43.65 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.5937
Blood Brain Barrier-0.9659
Caco-2 permeable-0.8957
P-glycoprotein substrateSubstrate0.7945
P-glycoprotein inhibitor INon-inhibitor0.6755
P-glycoprotein inhibitor IINon-inhibitor0.5633
Renal organic cation transporterNon-inhibitor0.8868
CYP450 2C9 substrateNon-substrate0.8417
CYP450 2D6 substrateNon-substrate0.8837
CYP450 3A4 substrateSubstrate0.6389
CYP450 1A2 substrateNon-inhibitor0.9222
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorNon-inhibitor0.9269
CYP450 2C19 inhibitorNon-inhibitor0.9203
CYP450 3A4 inhibitorNon-inhibitor0.9342
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9563
Ames testNon AMES toxic0.7696
CarcinogenicityNon-carcinogens0.9482
BiodegradationNot ready biodegradable0.9622
Rat acute toxicity2.5777 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9847
hERG inhibition (predictor II)Non-inhibitor0.7163
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (7.07 KB)
Spectra
SpectrumSpectrum TypeSplash Key
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-000j-0900000000-1f46f29c3d5dbc6c25f6
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0002-0901000000-3fc103447a71fd95cedd
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-016r-0895000000-4b0507fffd39d9fc075f
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-00mk-0952000000-ca2f735ea2244e1cb32e
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-004i-0901200000-cc68fda14967bfcd7357
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-004i-0900000000-70466cfb7e0692d073a0
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-004i-0900000000-b712dc39bbf605193fb4
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-0109000000-cdbfa33f16a571dd85ee
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-0209000000-8ec5c595eb6720c93c13
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-0201900000-1beeb0a912f1a6459dc3
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-2358900000-37a0ab9cc548b98b2f83
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-2932100000-ec655a6c81a371c81650
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-052b-6695200000-e40d09101ce3df762ac5
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-03fr-9510000000-38b96186711c5dede3ff
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-8921000000-7dd6cf5fc0d64316e8d4
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-206.7576126
predicted
DarkChem Lite v0.1.0
[M-H]-176.18422
predicted
DeepCCS 1.0 (2019)
[M+H]+207.1875126
predicted
DarkChem Lite v0.1.0
[M+H]+178.0796
predicted
DeepCCS 1.0 (2019)
[M+Na]+207.3675126
predicted
DarkChem Lite v0.1.0
[M+Na]+184.1802
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Nucleotide
Organism
Enteric bacteria and other eubacteria
Pharmacological action
Yes
Actions
Binder
Curator comments
Lincomycin binds the 23S rRNA within the 50S ribosomal subunit to interfere with protein synthesis.
In prokaryotes, the 23S rRNA is part of the large subunit (the 50S) that joins with the 30S small subunit to create the functional 70S ribosome. The ribosome is comprised of 3 RNAs: the 23S, the 16S and the 5S ribosomal RNAs. The 23S and the 5S associate with their respective proteins to make up the large subunit of the ribosome, while the 16S RNA associates with its proteins to make up the small subunit.
References
  1. Verdier L, Bertho G, Gharbi-Benarous J, Girault JP: Lincomycin and clindamycin conformations. A fragment shared by macrolides, ketolides and lincosamides determined from TRNOE ribosome-bound conformations. Bioorg Med Chem. 2000 Jun;8(6):1225-43. doi: 10.1016/s0968-0896(00)00081-x. [Article]
  2. Kouvela EC, Petropoulos AD, Kalpaxis DL: Unraveling new features of clindamycin interaction with functional ribosomes and dependence of the drug potency on polyamines. J Biol Chem. 2006 Aug 11;281(32):23103-10. doi: 10.1074/jbc.M603263200. Epub 2006 Jun 7. [Article]
  3. Kostopoulou ON, Papadopoulos G, Kouvela EC, Kalpaxis DL: Clindamycin binding to ribosomes revisited: foot printing and computational detection of two binding sites within the peptidyl transferase center. Pharmazie. 2013 Jul;68(7):616-21. [Article]
  4. Matzov D, Eyal Z, Benhamou RI, Shalev-Benami M, Halfon Y, Krupkin M, Zimmerman E, Rozenberg H, Bashan A, Fridman M, Yonath A: Structural insights of lincosamides targeting the ribosome of Staphylococcus aureus. Nucleic Acids Res. 2017 Sep 29;45(17):10284-10292. doi: 10.1093/nar/gkx658. [Article]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Binder
General Function
Not Available
Specific Function
Functions as transport protein in the blood stream. Binds various ligands in the interior of its beta-barrel domain. Also binds synthetic drugs and influences their distribution and availability in...
Gene Name
ORM1
Uniprot ID
P02763
Uniprot Name
Alpha-1-acid glycoprotein 1
Molecular Weight
23511.38 Da
References
  1. Gwilt PR, Smith RB: Protein binding and pharmacokinetics of lincomycin following intravenous administration of high doses. J Clin Pharmacol. 1986 Feb;26(2):87-90. doi: 10.1002/j.1552-4604.1986.tb02911.x. [Article]
  2. Son DS, Osabe M, Shimoda M, Kokue E: Contribution of alpha 1-acid glycoprotein to species difference in lincosamides-plasma protein binding kinetics. J Vet Pharmacol Ther. 1998 Feb;21(1):34-40. doi: 10.1046/j.1365-2885.1998.00111.x. [Article]

Drug created at August 29, 2007 21:12 / Updated at January 02, 2024 23:48